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ELEGANT SUPPORT CRAFTED FOR EVERYDAY CONFIDENCE

Step into refined comfort with the Rosie Orthopedic Boots, designed for women who value both timeless style and lasting support. With meticulous handcrafted detailing, a cushioned anatomical insole, and a sleek minimalist silhouette, these boots deliver all-day ease without compromising on elegance. Whether you're dressing casually or elevating a smart-casual look, Rosie offers the perfect blend of sophistication and orthopedic performance.

Orthopedic Comfort for Every Step: The padded anatomical insole supports the arch, reduces pressure, and provides soft cushioning—making long days of standing or walking noticeably more comfortable.
Effortless Fit & Everyday Convenience: A practical closure system allows for quick on-and-off wear, offering a secure, supportive hold around the ankle without fuss.
Confidence With Every Step: Built with a stable heel and a non-slip sole, the Rosie boots deliver reliable traction and balance on a variety of surfaces.

Specifications

Material: Soft, breathable vegan leather
Sole: Padded anatomical orthopedic insole
Fit: Wide Fit, Please choose 1 size up for an optimal fit.

Not happy with your order? Not to worry! We stand by the quality of our products.

If you are not satisfied with your purchase for any reason, you can return it always for a full refund or exchange.

Have questions about shipping? We’re here to help! Send an email out to our customer support team info@madisson-newyork.com

Order before 23:59 and we will send by tomorrow!

Making sure you receive assistance is a top priority for us!

If you still need help, we are available 24/7!

Reach out to our dedicated customer support team at the 'contact us' page

or email us at info@madisson-newyork.com

We're here to help with any questions or concerns you have.

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WHY CUSTOMERS 💗 Madisson

Excellent

4.8

/ 5

1,634+ reviews from satisfied customers.

such a cute boutique!! love how unique the styles are, and the quality is amazing. the owners are so sweet too, they really care about their customers 🥰 such a cute boutique!! love how unique the styles are, and the quality is amazing. the owners are so sweet... such a cute boutique!! love how unique the styles are, and the quality is amazing. the owners are so sweet too, they really care about their customers 🥰

✔ Maddie L. | 01/10/2025

first time ordering & WOW, i’m impressed! the fabric is soft, the fit is spot on, and it arrived super fast. def coming back for more!! 🤩 first time ordering & WOW, i’m impressed! the fabric is soft, the fit is spot on, and it arrived super... first time ordering & WOW, i’m impressed! the fabric is soft, the fit is spot on, and it arrived super fast. def coming back for more!! 🤩

✔ Chloe S. | 03/01/2025

These mary janes are fantastic. They’re stylish, comfortable, and really well made. I was a bit hesitant to order online, but I’m so glad I did. The fit is perfect, and they’ve quickly become my go-to pair for everyday wear. These mary janes are fantastic. They’re stylish, comfortable, and really well made. I was a bit hesitant to order online,... These mary janes are fantastic. They’re stylish, comfortable, and really well made. I was a bit hesitant to order online, but I’m so glad I did. The fit is perfect, and they’ve quickly become my go-to pair for everyday wear.

✔ Lori B. | 12/08/2024

Beautifully made and very comfortable. I was worried about ordering shoes online, but they fit perfectly. Great quality, and the style is even better in person. Highly recommend! Beautifully made and very comfortable. I was worried about ordering shoes online, but they fit perfectly. Great quality, and the... Beautifully made and very comfortable. I was worried about ordering shoes online, but they fit perfectly. Great quality, and the style is even better in person. Highly recommend!

✔ Amelia W. | 01/14/2024

i never write reviews but omg these boots?? so lightweight, so comfy, and they look amazing!! wore them to brunch and got so many compliments 🥰 i never write reviews but omg these boots?? so lightweight, so comfy, and they look amazing!! wore them to brunch... i never write reviews but omg these boots?? so lightweight, so comfy, and they look amazing!! wore them to brunch and got so many compliments 🥰

✔ Sienna J. | 02/09/2024

had to exchange for a different size and wow, the process was sooo easy!! the owners were so kind and helpful, they really care about their customers. such a rare find these days 💕 will 100% be shopping here again! had to exchange for a different size and wow, the process was sooo easy!! the owners were so kind and... had to exchange for a different size and wow, the process was sooo easy!! the owners were so kind and helpful, they really care about their customers. such a rare find these days 💕 will 100% be shopping here again!

✔ Holly T. | 12/20/2025

A FINAL FAREWELL

Hi, I’m Isabelle — founder of Madisson New York.

After many beautiful years, I’m closing the boutique as my mother Grace is beginning to grow older and seriously unwell, and it’s time for me to care for her.

With a heavy heart, I’m holding our Final Sale — up to 70% OFF to clear everything out. Once an item is gone, it will not return.

💗 Thank you, truly, for all your support.

Back to Orthopedic Boots

Frequently Asked Questions

We know how tricky sizing can be — especially if you have wider feet or deal with bunions or foot pain. At Madisson, our shoes are true to size and designed with comfort in mind. You’ll also find real fit tips and customer reviews on every product page. Still unsure? Our team is just an email away.

Of course! Once your order leaves our warehouse, we’ll email you a tracking link so you can follow it every step of the way. We’re always here if you need help along the journey

Yes, standard shipping is completely free within the United States — no hidden fees, just comfort delivered to your door.

You can pay safely with any major credit card. Your payment is 100% secure and fully insured — so you’re always protected.

We design for women who value comfort and style. Our shoes & sandals are lightweight, supportive, and flattering — perfect for daily walks, family outings, or just feeling confident at home. Thousands of women trust Madisson because we truly understand what your feet need.

We believe in our shoes — and we believe in earning your trust. That’s why Madisson offers a lifetime return policy. If your shoes don’t feel quite right, even after weeks or months, you can return them — no pressure, no deadline. We’ll make it right.